70931-12-3Relevant academic research and scientific papers
PURINES. XXI. SYNTHESIS OF ADENINE 1-OXIDES CARRYING AN ALLYLIC SIDE CHAIN AT THE 9-POSITION
Fujii, Tozo,Inoue, Isao,Itaya, Taisuke,Saito, Tohru
, p. 3443 - 3446 (2007/10/02)
9-Allyladenine 1-oxide (3) has been prepared from 1-ethoxyadenine (6) in 58percent overall yield through an unequivocal synthetic route.The route consists of an initial allylation of 6 with allyl bromide and Et-O bond cleavage of the resulting 9-allyl-1-ethoxyadenine hydrobromide (7) by treatment with boiling pyridine.Replacement of allyl bromide by 3-methyl-2-butenyl bromide in the above reaction sequence afforded 9-(3-methyl-2-butenyl)adenine 1-oxide (9) in 59percent overall yield through the 1-ethoxy derivative 8.Keywords - 1-alkoxyadenine; allylation; nucleophilic attack; dealkylation; N-oxide; catalytic hydrogenolysis; alkylation; UV; NMR
